Booked! But return to States Thanksgiving Wed, - Bad Idea?

We have always flown nonstop in previous years, and the international terminals are always pretty calm....but we are stuck a one-stop trip this time through Miami, landing in Chicago after 11PM Wed night, and will be very anxious to see the kids. Am I setting us up for disaster, or am I overthinking it?

You're not over-thinking it at all...while most Thanksgiving airport traffic IS Domestic....you are looking at the posibility of bad weather, and the ripple effect it has on the Eastern US airports- how many times have we seen news reports of all the people hung up in airports trying to " get home for Thanksgiving" ??
But- my bigger concern would be
clearing Customs in Miami. You can run into long delays there no matter what day of the year it is... it's one of the worst US locations, especially with flights from the Caribbean and/or South America.

We did the Miami layover to Chicago on the night before Thanksgiving about 4-5 years ago. Also arriving late in the evening from Miami. From what I recall, it was actually surprisingly uneventful. I expected travel at that time to be a nightmare and it wasn't. I chalked it up to people traveling to their Thanksgivings already being at their destination by that time the day before.

Thanks, everyone. I think we will chance it...now we need to decide if we want 1 1/2 hrs in Miami or 3.....it will be dinnertime - and after a week of Couples we'll be hungry - I hear there is a tasty Cuban Restaurant there. Maybe we will need the extra time eat? Any suggestions?/ Food Reviews?

Thanks, everyone. I think we will chance it...now we need to decide if we want 1 1/2 hrs in Miami or 3.....it will be dinnertime - and after a week of Couples we'll be hungry - I hear there is a tasty Cuban Restaurant there. Maybe we will need the extra time eat? Any suggestions?/ Food Reviews?

Personally, I'd do the 3. You never know if you may be delayed getting out of MoBay. We were delayed an hour once out of MBJ and BARELY made our connecting flight in Miami because of it. Even with no delay, I say 90 min layover would be a minimum just due to the process of immigration, customs, rechecking bags, going through security again and then because the Miami airport is SO BIG. It takes time.

We usually go for the 3-4 hour connection. Miami is a huge airport, but it's not as bad as everyone usually says. They have an enormous immigration and customs department and it's usually run pretty efficiently. Plus, there are a bevy of great little Cuban restaurants in the airport. (Try a media noche sandwich. or black beans and rice with fried plantains. MMMMMM....)

On the off chance that you DO get in earlier, you can always try to hop on an earlier flight. (We've done that before.) Just be aware that your bags will be checked on the later flight, so you'll have to go back to the airport to get them.